


For the Ecstasy

by Minxchester (ComeAlongPond14)



Series: A Criminally Hot Love Story [16]
Category: Supernatural
Genre: Dirty Talk, Flashbacks, M/M, Memories, Multi, Nail Polish, Sharing, Teasing, Threesome, Threesome - M/M/M
Language: English
Status: Completed
Published: 2018-11-02
Updated: 2018-12-13
Packaged: 2019-08-14 17:53:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 7,333
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16497413
Author URL: https://archiveofourown.org/users/ComeAlongPond14/pseuds/Minxchester
Summary: “He asked if we were exclusive, or inclined to share.”Title for this installment from "S.E.X." by Nickelback. ;)





	1. Chapter 1

**Author's Note:**

> So much like the part where Gabe entered the story, this is a two-chapter installment. Partially due to the length of chapter 2, and partly because I initially needed votes before choosing our roommate.

Gabriel had gotten his hands on some clear-coat nail polish that had silver and gold sparkles in it, and he appeared to be in love. Sitting at the little hotel room dining table, he was carefully applying a final coat, examining how his nails flashed in the crappy florescent lighting with evident pleasure as he turned his hand back and forth. Across from him, Sam was reading, while Dean and Cas were curled in the massive bed together, examining rope play suggestions and knot tricks online.

Cas pointed one out wordlessly, smirking in approval, and Dean grinned back at him, leaning over to nuzzle a kiss against the smaller man’s jawline. “That looks like a more elaborate version of the first time I ever tied Sammy up. Good taste, angel.”

Sam looked over at his brother curiously, raising his eyebrows and smiling fondly.. “You talking about at Stanford? Or a non-sexual instance from when we were kids?”

Dean barked out a laugh at the distinction between the two types of memories. “No, I mean a very sexual time. You remember? Your roommate walked in on us while I was tying your dick up for fun.”

Sam chuckled, finally setting his book aside in admission of complete distraction. “Oh, right. ‘Fun.’ Torturing me on purpose, more like.”

Dean merely shrugged, unapologetic and very clearly pleased with himself, and Gabe looked up from testing that his fingernails were good and dry. “What’d the roommate do? When he walked in on you guys?”

The question made Dean’s grin widen wickedly, and Sam rolled his eyes, giving his lover a slow-burning, smug smile. “He asked if we were exclusive, or inclined to share.”

Cas looked up curiously at that point, as hooked on the story as his fellow submissive, and Gabe tilted his head, eyes sharpening. “And were you, at that point?”

Dean shot him a bemused look. “Dude, our first kiss was over Cassie Robinson’s shoulder. We were  _ all _ about the sharing, right from the start. That poor kid’s eyes got bigger than dinner plates by our reaction to him askin’--I just hopped up off the bed, walked over and kissed him. He looked like he thought he was about to witness a breakup, the way he jumped and turned to see if Sam was pissed at me for doin’ it.”

Sam nodded, reclining back in the chair and rubbing a hand leisurely up his inner thigh, warming to the recollection. “Far from it. I sat up and started jerking off, with the rope. I asked him if he wanted to join us, and shocker--he said  _ fuck yes _ .” Sam shifted to the edge of his seat, and Gabe didn’t hesitate, setting aside the nail polish and sinking to his knees in front of Sam and rubbing his cheek along the taller man’s muscular thigh. “That was my first time topping with a guy. With Dean or anyone else we played with, I was usually the bottom.”

Cas licked his lips, eyes hungry and eager like they always got when he knew that they’re were going to hear a filthy story. “Did Dean fuck him, too?”

Sam shook his head, and Dean answered verbally. “Nope. I talked. I asked him questions. I got that sweet, shiverin’ little twink to admit that he’d been lustin’ for Sammy’s dick from the minute they moved into that dorm room. And then I talked Sammy through givin’ the boy a pounding that he would never forget.”

Both subs were enraptured. “Tell the whole story. Every dirty detail,” Gabe begged, and Dean laughed, trading a knowing look with Sam. 

“Tell ya? Or....should we recreate the experience for you?” At the looks they got for that suggestion, Dean nodded smugly. “‘S what I thought. C’mere, you adorable, needy bitch.”

Gabe hopped up from the floor immediately, kicking off his boxers and settling on his stomach on the bed. At Dean’s beckoning, Sam followed his lover, resting one knee on the mattress and running his hand soothingly up and down Gabe’s back as he waited for Dean to start speaking.

“Well, first things first...had to teach Sammy all the tricks for holding some still and fingering their pretty hole open enough to take a cock as big as his...”


	2. Better All Together

**Summary for the Chapter:**

> "Dean had to laugh at his stunned expression. 'It’s about time you learned to put this monster dick to its full and proper use, Sammy. Hell, I knew when you were 15 that you’d grow into a cock that’d make anyone squirm...but you’re even bigger than I imagined you’d be.'"

**Notes for the Chapter:**

> That took waaay too long to finish. Editing is rough; I promise to read over it again tonight and mend typos.

“Dean.”

“Mhm.”

“Dean....what the fuck are you doing.”

Dean smirked, dark jade eyes flicking up to meet Sam’s gaze along the impressive length of the younger man’s muscular torso. Sammy had really come into his lanky body as he headed into his 20s. “Seems to me that I’m usin’ the last foot or two of this rope to tie your dick up like a pretty little present, just for me.”

“....yes, but _why_ are you--oh, shit...” Whatever protest Sam had been attempting to offer was cut off as he moaned, head falling back in surprise at the surge of pleasure.

“That’s why...good boy, Sammy, spread your thighs nice and wide...show me those nice, smooth-shaved balls.”

“Sh-shut up....I only did that cause--”

“--cause I told you to, and you’re my very good boy. Now, hush, and focus on the sensation of the rope against that lovely, soft skin...”

Sam whined quietly, but obeyed like he always had and always would, dropping his head all the way back to rest against the bed with a hoarse moan. “Is that--are you--”

“I’m rubbin’ the rope over your taint and hole, yes. Don’t it feel damned  nice?” When Sam could only nod, choking on his own moans and gasps, Dean grinned smugly. “I knew you’d appreciate some of the tricks I’ve learned...”

Sam reached a shaking hand toward his dick, and Dean promptly batted his hand away. “Nuh-uh. Let me torture you for a little while, first...”

“So you admit it’s torture.”

“But it’s _nice_ torture. Don’t lie, you’re lovin’ this.” Sam couldn’t answer, and Dean’s smirk widened, aware of his victory. “Be good and take it, and I’ll let ya fuck me later.”

Sam started up a little at that statement, staring down at him. “Wait, but--”

Dean had to laugh at his stunned expression. “It’s about time you learned to put this monster dick to its full and proper use, Sammy. Hell, I knew when you were 15 that you’d grow into a cock that’d make anyone squirm...but you’re even bigger than I imagined you’d be.”

Sam’s blushing. “And you....you want--”

“Fuck yes. Told ya, baby, I’ve played the field. Now, I’ve never had anyone half as hung as you, but I think I’m more than good with lettin’ my baby brother break all my existin’ records. And I wanna teach you how to make a fella scream."

Sam shudders. “You do sound _really_ fucking good when you come...”

Dean had Sam’s cock half down his throat when the bedroom door abruptly opened. A slightly younger Korean boy was standing there with his book bag hanging off one shoulder, staring at them with owlish shock, the door still open at his back.

Sam jumped, yanking the covers over them enough to accidentally cover Dean’s head for a second before Dean pulled up. He simply raised his eyebrows at the newcomer curiously, as if he wasn’t buckass naked and very obviously in the process of sucking Sam’s dick. “You Sammy’s roomie?”

The boy nodded, still looking stunned. “I’m, I’m sorry, I didn’t--usually we put a sock on the door, or whatever--I didn’t realize--”

“‘S all good, handsome,” Dean assured him, laughing as Sam kicked at him for his cheek. “What, come on, you covered up your horse dick. I got no shame.”

“Can you be nice, please?” Sam retorted, still keeping the sheet over himself. “You’re traumatizing Kevin, put that thing away.”

Dean eyed Kevin, who was struggling valiantly and visibly to maintain eye contact and not let his gaze slide downward. “Y’know, Sammy, I don’t think it’s trauma he’s feelin’. I know that look--Kevin, was it?” At his shy nod, Dean chuckled, soft and full of dark promise. “I’ve seen that sparkle plenty of times, in plenty of pretty eyes. Go on and say it, Kev, come on. Give Sammy a nice little shock.”

Kevin swallowed, clearly feeling cornered but not seeming to resent that fact. He pushed the door shut behind himself at last, which makes Sam go still, staring at him with rapt attention and mild expectation.

“Are--are you--is this your boyfriend?”

Sam huffed; they never used words like that between the two of them. “I guess. I mean, he’s the only person I consistently fuck, so....sure.” Dean reached back to rub his thigh comfortingly, and Sam sighed, finally relaxing. “Look, Kevin--”

“Do you--do you guys ever share?” At Sam’s dumbstruck look, Kevin turned brick-red red. “I just mean--like, bringing someone else in--”

“Our first hookup was a threesome,” Dean replied, his grin widening wickedly as Sam choked on a protest. “A girl, that time, but I was _just_ tellin’ Sammy that he needs to play with a guy next. I gotta teach him the proper techniques for makin’ a twink lose his mind.” He wiggled his eyebrows, giving the younger man an overly-obvious once-over. “You a twink, Kevin?”

“Dean,” Sam growls, eyes rolling. “Do not proposition my roommate, that’s just--”

“I’ve only, um, been fucked once before,” Kevin stuttered, still focused on Dean more than Sam. “It was a strap-on, too, not...not a real...a real one.”

“The plot thickens.” Dean shifted to the edge of the bed, no shame for his erection bobbing against his belly, and Kevin couldn’t help finally looking down at it, his brown eyes darkening to near-black. Sam sat up, watching this exchange. “It was a girl?” Kevin nodded, and Dean grinned wider. “Well, the real deal’s better, trust me.”

Dean stood then, and neither of the other two men said a word as he prowled forward, leaning in and kissing Kevin lightly. The book bag dropped from his shoulder with a thunk, and Kevin seemed to almost fall back against the door, his hands plastered to the wood as Dean crowded into him, biting at his bottom lip tauntingly before finally releasing him.

Kevin’s eyes flashed past him, staring worriedly back at Sam, but Sam was smiling now too, realizing that Dean had the situation fully under control. He sat up, pushing aside the blanket and slowly closing one hand around the rope that was still twined around his cock, stroking leisurely. Kevin spotted the rope and went still again, his mouth opening in a surprised little O. “Bondage, too?”

Sam nodded, laughing softly. “Dean’s idea, of course. He wants me to try everything once....” He looked down, toying with the rope against his skin. “And I definitely like this one.”

Kevin nodded shallowly, looking from the rope back to Dean’s lips, then back to Sam, who smiled back at him kindly as he dropped his legs off of the side of the bed, taking pity on his roommate. “You wanna join us, Kevin? I don’t mind, promise--I was only protesting because I didn’t want Dean to freak you out, if you weren’t into it.”

Kevin nodded hastily, no hesitation whatsoever in his voice or his body language. “I--yes. Fuck yes, please.”

_* * *_

_Gabriel snorted, looking over his shoulder at Sam as his lover leaned slowly over him, peppering kisses down the length of his spine and over the swell of his ass. “Doubt anyone with a functional brain could refuse once they saw your cock...how’d you take him?”_

_“Same way he’s gonna take you, once we get to that part of the story,” Dean interjected, accommodating Cas as the brunette set the laptop aside on the floor and then moved to curl into his lap. “But you interruptin’ will drag out the fun.”_

_Gabriel stuck out his tongue at that, but he compliantly quieted down, listening as Sam continued stroking and massaging his body lazily_.

* * *

“Clothes off, Kev,” Dean instructed, slowly walking backwards until he could grab Sam’s desk chair. He pulled it away from the wall and sank into it, crossing his legs. “Let’s see the canvas we get to work with.”

Kevin blushed darkly, but he obeyed at once, removing his shoes, shirt, jeans, socks, underwear, and folding them neatly on the dresser nearest to him, eyes staying locked on the brothers. He was already hard, pre-come glistening at the slit.

Dean beckoned him forward, and Kevin padded toward him, stopping in front of Dean and then glancing at Sam, who gestured for him to keep his focus on Dean.

“You ever touch a guy at all? Or let one touch you?” At Kevin’s head shake, Dean grinned. “Good. Gonna absolutely blow your mind, sweetheart....” Placing his hands at Kevin’s hips, he drew him in and kissed just below his belly button, then continued making his way downward, back and forth over the younger man’s belly, until his lips were beside Kevin’s cock. Dean gave the head one small, gentle kiss, making Kevin moan, and then he nudged the younger man toward the bed.

“Give Sammy a proper kiss, too, and then we’ll get started, handsome.”

Kevin stumbled over immediately, and Sam caught him, supporting him as Kevin leaned in. They kissed lightly, delicately, like they aren’t both naked and hard and aching. Like a pair of kids on a first date, shy--and definitely not about to fuck hard.

Once they broke apart, Dean nodded, his fingers dancing absently over his own thighs as he watched them with ravenous eyes. “Lie on your belly on the bed, Kevin. I’m gonna teach Sammy how to open up a gorgeous twink like you...it’s gonna take some time. You need to be good and ready to take him.”

Kevin’s eyes dropped to Sam’s dick, and he nodded, blushing again. “Yeah. I--I believe that.”

_* * *_

_Cas giggled, and Dean glanced down at him with eyebrows raised in question. Cas shrugged in response, giving Sam a fond smirk. “Bet he had a second of re-thinking, then. I remember the first time I saw Sam’s cock...no matter how desperate you are to get fucked, that_ **_is_ ** _an intimidating sight_.”

* * *

Sam reached out to draw Kevin in for another swift kiss, guiding him to sit first, beside him. “Don’t worry. I’m going to go very slowly; Dean’s going to make sure we take good care of you.”

Kevin bit his lip, then grinned, nodding as he turned and rolled behind Sam, stretching out on his stomach on the bed and then inhaling deeply. “I’ve....I’ve had to resist the urge to come lay here before,” he confessed, as if not looking at Sam made it easier to get the admission out in the air. “Wanted to know what you smell like...”

Dean’s grin was wolfish and feral. “And now you’re gonna know exactly how he smells, tastes, feels...you’re gonna be screaming his name before I’m done with you...”

He moved his chair to have a nice clear view of them both, and Dean nodded at Sam. “Get up on your knees, Sammy. Put a pillow under his hips, and you kneel between his legs.

_* * *  
_

_Sam followed the instructions to the letter as they were given in the story, turning to move between Gabe’s spread thighs and sliding a pillow underneath him._

_“I ain’t a virgin,” Gabe pointed out, his voice rich with amusement. “Don’t really need the ‘be gentle with me’ chivalrous treatment...”_

_“We’re showing you the story in real-time,” Dean shot back, grinning when Sam gave his submissive a sharp swat on the ass for his sass. “Shut up and let Sam seduce you.” Gabe merely laughed, surrendering, and Dean and Sam exchanged a grin as the blonde resumed the tale._

_* * *_

 

Once the pillow was supporting Kevin’s hips, another under his head and folded arms, he shivered. “I feel so exposed...and it feels good,” he whispered. “Sam...”

“You look absolutely gorgeous,” Sam told him, low and heated with arousal and pleasure. “Christ--I’ve seen _Dean_ like this, just exploring--haven’t gotten to fuck him yet. But right now....God, I see your hole and I just wanna....fuck.”

“You’re gonna,” Dean teased, leaning forward and licking his lips as he watched Sam eyeing the body spread out before him like it was a five course meal. “Let’s start out easy. Get one finger nice and slick, Sammy."

Sam grabbed the lube that they had been using earlier, warming a good amount between his index and middle fingers and then looking back at Dean, his eyes sparkling. “Keep going. I think he likes your voice as much as my touch.”

“I do,” Kevin admitted at once, laughing breathlessly and without shame. “Fuck, the two of you together...it’s way too hot.”

“Touch his hole, Sammy.” Dean’s voice had lowered, darkened. If it was a voice kink the pair of them wanted, then he could more than provide. “Rub the pad of your finger over him. Let him feel it...feel what’s comin.’”

Sam obeyed, just using his pointer finger, rubbing slowly over the pucker and letting out a low breath of pleasure as Kevin moaned at the first touch, his toes curling and hips pushing back toward Sam in silent need. “Keep him still, baby,” Dean purred. “Keep those hips of his down against the pillow...’s gonna be more comfortable for ‘im.”

Sam complied, placing his other hand on Kevin’s lower back and pushing down gently. Kevin whined in response, turning his face into the pillow. “Fuck....God, I _knew_ you were strong, but....goddamn...”

Dean laughed quietly. “He’s broken headboards before, takin’ my cock. Bet those nice, long fingers of his are gonna leave bruises on your thighs, huh, Kev? And you’re gonna love ‘em...”

“Yes,” Kevin whimpered, biting at Sam’s pillow as if the thought of it was too much and not enough, both at once. “Yes, please....want that.”

Sam’s voice is heated and unsteady, his usual rock-solid control evaporating by the second. “Dean--more, keep going. What’s next.”

Dean cocked his head, watching Sam’s fingertip rubbing and rolling over the clenching sphincter. “The finger, or your tongue. Somethin’ goes inside....starts loosenin’ him up for real.”

Sam didn’t hesitate, withdrawing his finger and shimmying downward to bring his face level with Kevin’s hips. Feeling the hot brush of breath against his entrance, Kevin groaned darkly. “Shit, _shit_ , you’re not--”

“He is,” Dean assured him, beaming with pride at his brother’s performance, and they spell he was clearly weaving over their companion. “Do it, Sammy. You’ll pick it up easy--it comes naturally...”

_* * *_

_“Okay, if you tell me that Sam fell into rimming like he was born for it--”_

_“He did.” Dean retorted, and Sam rolled his eyes, spanking his fingers down onto Gabe’s hole before dropping down to start eating him out, making the smaller brunette cry out._

_“Fucking--you didn’t spank_ **_him_ ** _, that wasn’t in the story--”_

_“You complaining?”_

_“Fuck no--oh, Jesus, yes--deeper--”_

* * *

Sam looked back at Dean, who nodded firmly, and no further urging was needed.

Sam dipped in, pressing the flat of his tongue against Kevin’s hole and sweeping upward. He repeated the motion as Kevin moaned his name in a broken, ravished voice, using his hands on Kevin’s lower back and one thigh to keep him pinned as Sam started testing out his options--licking, nipping, sucking, and thrusting his tongue inside once the rim loosened a little more, letting him in.

Kevin was twisting and writhing beneath his hands, unable to squirm away or wriggle closer, and his eyes found Dean’s, wide and near-black and utterly overwhelmed. “He _has_ to have done this before--”

“Only to me,” Dean replied, soft and tantalizing. “I’ve let him explore every inch of my body whenever he’s wanted to. But Sammy’ll tell you that doesn’t count--that’s just him and me, ‘s too natural. We were made for each other, we’re like puzzle pieces...but this, with you? Sam’s just that damned good at being _good_.”

Sam growled softly as he listened to Dean brag on him, and Kevin jerked in surprise at the sensation. “Shit! Oh, fuck, felt that--right through me--”

“Sam.” The younger man looked up, and Dean grinned savagely at the sight of his face. “Oh, baby...look at you. Fuckin’ wild. Think it’s time to get two fingers into him....you can keep lickin’ around ‘em.”

Sam nodded, looking dazed as he lifted his head. He sucked on two fingers noisily, making Kevin moan at the sound of it. His voice only got louder as Sam rubbed the slick digits over his entrance. His hole was opening more easily every minute, and Sam’s middle finger finally eased into him, not slowing until the middle knuckle was buried.

“Jesus,” Sam whispered, awe in his face and voice. “Dean, he’s on _fire_ in there.”

Dean merely nodded, watching Sam’s hand like he was riveted. “I bet. You can get the index finger in there, too, Sammy, find his--”

Kevin jolted up off of the bed, and Sam clapped his other hand back onto his ass, pinning him as Dean barked out a laugh. “Oh, fuck, baby boy, your fingers are just that long--go on, target his sweet spot. Show Kevin what me and Cassie taught ya...”

“You--want me to make him come?” Sam groaned, continuing to rub roughly over Kevin’s prostate as the smaller man whined and wriggled, trapped by Sam’s hand. Sam eased his pointer finger in alongside the middle digit, spreading Kevin’s entrance even more.

“Not just yet.” Dean ignored Kevin’s pleading whimper at his words. “Just keep rubbing it, on and off. It’ll open him up more...I wanna get four of your fingers inside before we start talkin’ about that cock goin’ in.”

Sam smirked. “Four, huh? You must be feelin’ sadistic today, De...”

Dean laughed, the sound soft and musical. “Far from it. You haven’t shoved that monster snake of yours up anyone’s ass before, and Kevin’s only taken plastic. Kev--was your girl real careful about preppin’ you first?”

Kevin nodded, shakily, against the pillow. “Y-yeah. Took a freaking long time...”

“Exactly.” Dean winked at his brother. “Forget the pornos we’ve watched, baby, and don’t compare it to how quickly I always go from wanting one to four fingers. Hell, I got no gag reflex, and you’ve choked me on your cock. So we gotta be nice and gentle with our playmate...”

* * *

_“Think it’s up to two fingers in the story, now, Sammy.”_

_Sam drew back from Gabe’s ass to stick his tongue out at Dean, . “Maybe I like his taste too much. ‘Sides, he won’t take as long to open as the storyline would require, so unless you wanna skip over the fucking ten minutes I spent just loosening Kevin up...”_

_“Oh God, please don’t.” Gabe gave a strangled laugh, his entire body trembling. “I got the stamina for it. Fuck, take ten goddamn minutes to lick me open and only give me two fingers....”_

_Dean grinned. “Why, that’s the most submissive, masochistic thing I’ve ever heard you say. Knew you had it in you. Such a good bitch....”_

* * *

Sam complied with Dean’s instructions perfectly, slowly twisting and turning his hand to get his middle and index fingers all the way into Kevin’s ass as the younger man rocked and groaned, kept firmly in place by Sam’s other hand on his back. “Won’t he come if I keep targeting his prostate?” Sam asked softly, his brow furrowed as he concentrated on his task, and Dean chuckled fondly at his brother’s ever-attentive and ever-learning nature.

“Not necessarily, but that’s his job to know...Kev, baby, if you get close--”

“Won’t.” Kevin’s voice was little more than a breathless whine by that point. “It’s just--torture, good torture, won’t come, promise--”

Dean’s eyes were dark and hungry as he leans forward. “Christ, you’re a born bottom. Perfect little plaything for me to teach Sammy with....hell, this is better than if he practiced by fucking _me_. I can take it no problem, but I’m a toppy bastard.”

Sam smirked over at Dean knowingly. “‘S why I haven’t even bothered asking yet, honestly. I knew you’d want me to learn eventually, but it’d be all on your terms.”

Dean licked his lips at that. “Start on the ring finger, Sammy. Curl ‘em in like this--” He demonstrated, raising his hand and bending the index and ring fingers toward one another in front of the middle. “--and tuck your pinky in with your thumb for now.”

_* * *  
_

_Sam worked the third finger into Gabriel, smacking his ass as the brunette tried to push back against him in order to impale himself faster. “Behave, you’re playing the shy virgin with the too-tight ass, here.”_

_Gabriel snorted. “You remember the first time we fucked, sugar? Ain’t a damn shy thing about me.”_

_In retort, Sam shoved all three digits inside at once, striking his prostate, and Gabe bucked back with a howl as Dean merely cackled at his brother’s response and continued._

_* * *_

Kevin was visibly struggling to lie still and take it now, his thighs flexing together and then apart again, as if he couldn’t decide whether he wanted more, or less. “God, Sam--your fingers, so thick--feel fucking amazing....”

Sam preened at the praise, giving Kevin’s prostate another rewarding little rub. “Helps that you’re so damn snug, sweetheart...fuck, can’t believe I’m actually fitting three in you.”

“And it’ll only get better, too,” Dean purred. “Pull back out, Sammy, and then let your pinky rub along the rim with the other three. Let his hole get the idea of four and start adjustin’....”

Sam slowly withdrew his hand, chuckling as Kevin groaned low in protest at the emptiness that’s left behind. “Patience, baby, he’s coming right back...”

Sam followed Dean’s order, letting all four of his fingers rub along the swollen rim, and he grinned widely at the noise that Kevin made when he felt them all. “Christ, De, how do you resist just shoving inside?”

Dean wiggled his eyebrows, perching right at the edge of the chair in order to e able to watch as Sam took a little more initiative, starting to ease all four in. “I usually don’t. But virgins get special treatment, Sammy...gotta take care of that sweet hole. Make it all good for ‘im, make it somethin’ he’ll come back to you for, again and again.”

Kevin let out another whine, legs flexing wider apart as Sam’s fingers slowly sink in to the first knuckle. “Please, yes. Please tell me we can do this again...”

Sam snorted. “You wanna be fuck buddies with your roommate? I’m down...”

_* * *_

_“I appreciate this story in full, but you may as well time-skip a bit on getting four fingers into him,” Gabe panted out. “It’s not even gonna take half as long for me.”_

_“Well, you ain’t wrong,” Dean conceded, petting his hand through Cas’ hair as his lover mouthed his way down Dean’s torso, movements semi-uncoordinated from his focus on the story. “Alright, bitch, you win....”_

* * *

Kevin was a shuddering, limp mess by the time that Sam finally had all four of his fingers twisting and scissoring inside of him, moaning and almost crying from the pleasure and the building, burning need. Dean stood up at last, moving to the bedside and reaching out to tilt Kevin’s face up in order to lean in and kiss his lips delicately. “Think you’re about ready, champ...you still wanna feel Sam’s big cock inside you?"

Kevin made a strangled noise and nodded roughly, his beautiful dark eyes fluttering closed. “Please. Please, l-let me--let him split me open--”

Dean met Sam’s gaze over the younger boy’s unruly black hair, and he grinned when he saw that Sam looked about ready to combust. “You heard the man, Sammy. You gonna impale him on that footlong of yours, or what?”

Sam pushed himself up at once with the hand that wasn’t four-fingers deep in Kevin’s ass, and Dean met him halfway, kissing and biting at Sam’s lips until Sam is whimpering softly himself.

Dean carefully started puppeteering his brother more directly, gently arranging Kevin so that the pillows had his hips much more prominently raised and ready, exposing his now-gaping hole nice and clearly. Kevin whined as cool air moved over the sensitive tissue, clenching around Sam’s fingers as they slid free.

“Lube up again, Sammy,” Dean instructed, voice rough and eyes locked on their playmate. “Make sure you’re good an’ slick for that cute virgin cunt...”

Kevin cursed at the dirty talk, thrusting backward into air, his hole clenching on air in reaction. Dean grinned wide. “Oh, I knew you’d like that. Don’ worry, Kev, Sammy’s comin’ for ya...”

_* * *_

_Sam drizzled a glob of lube onto his cock and leaned forward over Gabe’s back, rutting leisurely and letting the smaller brunette feel the long, hard line of his erection sliding wetly along the seam of his ass. Gabe groaned filthily, bracing himself to push back in encouragement before whining as Sam once more effortlessly pinned him back down, his broad hand between his lover’s shoulder blades._

_“Cruel,” Gabe pouted, absolutely no heat in his voice. “You tease him, too? Bet he fainted at the first touch of that fuckin’ hose of yours...”_

_Dean just laughed, pushing Cas down the last few inches in order to sink his cock into his sub’s waiting and willing mouth. “Quite the contrary_....”

* * *

Sam didn’t ask or check again with Dean; once his dick was glistening with the lube, he moved back between Kevin’s thighs and humped his ass slowly, like he was getting used to the heat of the smaller man’s body against his shaft. Kevin gave another strangled cry, trying to spread himself wider, his eyes flying up to Dean’s face as if he could not longer manage to speak--as if he needed Dean to do the talking for him.

Dean smirked knowingly, leaning over him to lick over Kevin’s lips and then lap his wayinside, teasing the younger man’s tongue with his own. “When he starts pushin’ into you, try to meet the motion. Relax and breathe. Let him in for me, okay, sweetheart? I know you’re gonna be so fuckin’ good at this...”

“De.” Sam’s head fell back, eyes closed in indescribable ecstasy. “Can--is he ready? Fuck, please...I need it. Need to be inside him...”

Dean nodded at once, sliding around Kevin and moving to stand by Sam. He placed his hands delicately on his brother’s waist, grinning when that made Sam shudder harder.

“In you go, baby,” Dean whispered into his ear, lips brushing teasingly over the lobe. “Fuck that pretty pussy. See what all the fuss is about...”

He reached around Sam, grasping his cock and lining the head up with Kevin’s entrance. Sam thrust forward with a broken gasp, as if he couldn’t handle the heat of both Dean’s hands on him and Kevin’s hole around him, and he sank in several inches before stopping to drag in several long, deep breaths.

“Jesus--fuck--seriously--” Kevin sounded absolutely wrecked, his voice cracking intermittently. “God, _please_ , fuck me--move, God, you’re so huge, feels so damn good, please just--ream my ass--”

Dean gave Sam’s ass a playful swat, laughing when his brother just grunted in response. “Can’t let the man down, Sammy boy....you know how to do this. You fucked Cassie’s sweet little cunt, remember? And you’ve been balls-deep in my throat plenty’a times....same thing. Just slam on in, and give this mouthy boy of ours the poundin’ he’s beggin’ for.”

It was Sam’s turn to make a choked sound of incoherent need, and he obeyed Dean almost mindlessly. His hips shifted back toward Dean and then snapped forward again hard, burying his cock inside of Kevin. Both men give hoarse shouts of pleasure as Sam’s cockhead rubbed directly against Kevin’s prostate from the force of his first real thrust.

_* * *_

_Sam slammed inside of Gabe in pace with the story, not slowing down as he had with Kevin to let his lover adjust, and Dean momentarily paused speaking as Gabe reacted violently. He threw his hands out over  the bed, holding on for dear life as he was fucked brutally. Dean watched them greedily, now fisting Cas’ hair and sliding his mouth up and down Dean’s cock like he was nothing but a fleshlight._

_“Keep--talkin’--De--” Sam’s voice was barely above a snarl, nothing left of the shy boy from Dean’s story learning the ropes. “Talk--me off. Wanna--come in his ass--”_

* * *

“Christ, look at you go,” Dean purred, leaning around to watch Sam hammering into Kevin, his cock sliding wetly in and out, deeper with every forward motion. Sam’s hands were on Kevin’s waist just as Dean’s were on his, offering some support as Kevin more or less just bounced between the bed and the man fucking him, helpless and broken noises of pleading and praise falling from his lips. “You’re a fucking _stud_ , Sammy. ‘S it, we’re gonna go find us a nice bondage club....find some twinks with a size kink. See how long a line we get of needy little things, wantin’ to bend over and let you fill up their hungry little cunts...”

Sam made a noise like he was dying in the best possible way. He slammed in too deep, one last time, making Kevin howl as the older man came inside of him. Dean could already see smears of white edging out of the smaller man’s hole around the base of Sam’s dick--his brother’s load was already leaking back out, even as he fucked it into Kevin’s receptive, limp body.

Finally, eventually, Sam regained his equilibrium. He drew back, caressing Kevin’s back in gentle apology. “Hey--you still with me? Did I hurt you?”

Kevin merely gave a faint, borderline-hysterical laugh. “Not even slightly. I mean--yeah, I’m still with you. But not hurt. Just....God. Fucking blissful.”

Dean moved around to sit at Kevin’s head, stroking his sweaty hair back from his face tenderly. “You need help rollin’ over, handsome? Wanna make sure we get you off, too.”

Kevin blushed and giggled, pushing himself up just a little, not letting Sam slide out of him yet. “No worries. He fucked it right outta me...”

Sam peered over Kevin’s shoulder, surprised, and then he groaned softly when he saw that Kevin had come already, smearing it all over himself and the bedding. “Fuck, he came untouched, De...”

“He did, indeed.” Dean’s eyes glittered with dark pleasure and approval. “That’s damned high praise. Sammy’s horse cock really did it for ya, huh, Kev?”

The smaller boy grinned a little sheepishly, still blushing even as he enjoyed the praise. “Yeah. I--well, I actually came at the time that Sam did. From, uh, what you said....”

Dean’s grin widened, edged with vicious delight. “The whole size kink bit? You came without a hand on your dick, just ruttin’ between Sammy and the bed, imaginin’ him pumping your pussy full of all the come he’s got in that monster cock of his?”

Kevin nodded, too overwhelmed to speak the words himself, and Sam cursed quietly, visibly awestruck. Grabbing Kevin with unsteady hands, he tilted the Asian man’s face around to kiss him savagely, biting his way into Kevin’s mouth and swallowing his moans as he did. “Next time,” he whispered, and Dean licked his lips at the utter control and heat in his brother’s voice, reaching down to rub his own hard on soothingly as he listened to Sam growling possessively. “Next time, you’re gonna ride me. Gonna make you do the work to take the whole thing...”

_* * *_

_“Shit, why has no one brought this up before?” Gabe sounded offended even as he was panting, his entire body rocking against the bed and making the headboard slap against the wall slightly as Sam fucked into him, hard and deep. “You mean this entire goddamn time, I could have been the world’s most dramatic fucking size queen?”_

_“Oh, yeah, cause all this time you’ve been_ **_subtle_ ** _.” Dean grinned again, his eyes flashing with fire as he reclined back into the pillows, no longer controlling Cas’ movements. Cas was simply enjoying himself now, sucking and kissing down the sides of the shaft, over Dean’s balls, teasing his tongue further back toward Dean’s hole as he enjoyed the story and their banter. “I’ve always loved Sammy’s size,” Dean added, reaching over to thrust two fingers lazily into Gabe’s mouth, as if to hush him as Sam began speeding up his thrusts, crashing towards his climax. “First time it was just me an’ Sammy, no third person...he admitted to me that was the kinda porn he liked.” Dean grinned as Sam gives him a dark, hungry look over Gabe’s heaving body, nodding his agreement. “He loved seein’ tiny, slender things bouncin’ up and down on dicks that were way too big for ‘em...he told me once that he didn’t realize how big_ **_he’d_ ** _be, so he thought he’d end up being the twink.” Dean chuckled, giving his brother a smug ;ppl. “I mean, I’ll Daddy it up if he wants me to...but some days, there ain’t nothin’ better than gettin’ reamed so hard by that thing that you’re limpin’ for days afterward.”_

_Gabe finally came at that, and his clenching hole pulled Sam over the edge with him; Sam snarled as he came with his lover, biting at Gabe’s shoulder harshly._

* * *

Kevin was close to catatonic when Sam released him again, slumping forward into the bedding and whining softly when Sam carefully slipped his cock out of him. Dean stood, coming to lean over the drowsy boy, spreading his ass cheeks with his palms in order to examine Kevin’s fucked-out, dripping hole. “God, he filled you up good,” he purred, making Kevin moan happily.

Sam tugged at his brother’s arm, and Dean turned back toward him willingly, laughing as Sam shimmied around to lie on his back without disturbing Kevin’s sprawl. “You already came, Sammy, and you still need more? Insatiable...”

Sam shrugged, not embarrassed by his desire in the least. “I came, but you haven’t, and I’m still open from you torturing me before Kev got here. Fuck me, De...”

Kevin sat up a little then, regaining some strength at the prospect of more of a show from the pair of them. He shifted back against Sam’s headboard and watched them with hooded eyes, running his tongue over his bottom lip. “Fuck, yes, please do that. Wanna see it...”

Dean smirked at him, leaning over to kiss the Asian boy again, quick and hard, sucking briefly at his tongue. “Ya wanna see the guy who just reamed your ass takin’ it up his? Wanna hear how pretty Sammy screams for me?”

_* * *_

_“Is this part gonna be acted out, too?” Gabe interrupted, spent from his orgasm but still inescapably cheeky._

_Dean snorted, trading a look with Sammy. “Not this time ‘round. You gotta be_ **_real_ ** _good to earn that show...” Sam murmured, licking his way down Gabe’s body to gather up the smears of Gabriel’s release on his tongue. Cas shifted in place, settling up on his knees with his back against Dean’s chest, and the older Winchester tugged him easily down onto his cock, sinking into the brunette’s waiting body with a low groan of relief._

* * *

Dean made sure to make it fast; Sam didn’t need more prep, so Dean just slicked his own cock up and then pulled Sam over to the edge of the bed, pushing his legs in the air and shoving into him. Sam clutched at the bedding and howled with pleasure, the sounds punching out of him as Dean fucked into him hard and deep, his hands on Sam’s ankles to keep his legs raised as he pounded his ass.

Kevin watched them move with raw hunger in his youthful face, stroking his soft dick and groaning in sync with Sam as Dean finally came as well, burying himself to the hilt inside of his brother.

When Dean eventually drew back, he held out a hand to Kevin, who accepted it without hesitation and eagerly let the blonde guide him off of the bed onto his knees, kneeling between Sam’s spread legs. Dean fisted his hand in the kneeling man’s hair, controlling him as he pushed Kevin in close, forcing him to lick and suck Dean’s release out of Sam’s body.

_* * *_

_Cas cried out when  he felt Dean come inside of him, then immediately slid up off of his lap, twisting to face Dean and kiss him hard even as he pushes his ass into the air towards Gabe. The other brunette made a noise of delighted at that, letting Sam sit back up to mimic Dean’s position in the story, pressing Gabe’s face into Cas’ ass to clean him up with noisy wet slurps._

* * *

Kevin all but stumbled back to his feet to go curl back onto the bed, and Sam coiled himself around him, watching Dean with quiet gratitude in his eyes over the younger man’s shoulder.

“Please tell me you’ll be around often,” Kevin slurred, his voice getting softer as he drifted towards a hard-earned nap. “Like, I need that to be a weekly event, if not daily.”

“It’ll be more often,” Dean confirmed drily. “Only thing I care about in this world is makin’ him happy--” He nodded at Sam, even though Kevin’s eyes were closed and he therefore missed the gesture--“and sharing playmates is a damned good way of doin’ so.”

“He’ll be back,” Sam agreed, chuckling quietly. “Long as you and I are friends, Kev, he’ll be there too. We’re a package deal.”

“ _Quite_ the package, too,” was Kevin’s final mumbled response before he drifted off, and Dean barked out a laugh, winking at Sam as he rose to go leisurely dress himself.

“I’m gonna go get some food and bring it back. He’ll need the energy boost.” Dean smirked. “I get the feelin’ I’ll be able to skip on usin’ our motel money and crash here with you, huh, Sammy?”

His brother nodded sleepily, his hazel eyes closing gradually as well. “Don’t forget your pie.”

Dean’s eyes softened, and he leaned over Kevin to kiss his brother’s lips, sweetand short. “That’s my boy.”

_* * *_

_Gabe drew back with a happy hum, and Cas slumped to curl around Dean._

_“Kevin was fun,” Sam mused, reclining back on one elbow and stroking Gabe’s side. “I missed him for a while, after we took off.”_

_Dean smirked at his brother, shrugging. “Wonder if he’s ever seen our names on the wanted lists and realized what he’d dipped his toes into. He didn’t know we’re brothers then, after all.”_

_Sam snorted. “I’m sure he’s forgotten all about us. He was smart and pretty. No doubt he’d found something good for him.”_

_“I know we have,” Cas contributed, smiling as Sam reached out to draw him in for a sweet kiss in response to the words._

_Gabe cut in, his eyes twinkling wickedly. “Mm, but speaking of the most wanted list--”_

_Sam shot him a bemused glance. “You_ **_just_ ** _came, you cannot possibly be ready to go again.”_

_Gabe merely stuck out his tongue giving his Dom a cheerful middle finger. “Fuck you, my stamina is incredible. But no, I’m thinkin’ more that it’s time to plan our next big job. I’ve been doing some research on cutting the phone lines so we can get in and out without panicking over anyone calling the cops the instant we’re outta sight.”_

_Dean chuckled at the brunette’s ingenuity, leaning over the edge of the bed to grab the laptop and handing it over. “I love the way you think, you know that? Alright, let’s get down to business...I was thinking maybe we head down south for a little while...”_

**Author's Note:**

> Kevin was the overwhelming victory vote, this time around--but enough people did want both Chuck and Jack that it's safe to promise they will make appearances as well, either in this series or in other tales.


End file.
